Titre du document / Document title

A mild and highly convenient chemoselective alkylation of thiols using Cs₂CO₃-TBAI

Auteur(s) / Author(s)

SALVATORE Ralph Nicholas ; SMITH Robert A. ; NISCHWITZ Adam K. ; GAVIN Terrence ;

Résumé / Abstract

A mild and improved method for the synthesis of thioethers has been developed. In the presence of cesium carbonate, tetrabutylammonium iodide, and DMF, various alkyl and aryl thiols underwent S-alkylation to afford structurally diverse sulfides in high yield. Unprotected mercaptoalcohols and thioamines reacted chemoselectively at the sulfur moiety exclusively. An example of a one-pot, solid-phase synthesis of a thioether is also described.

Revue / Journal Title

Tetrahedron letters   ISSN 0040-4039   CODEN TELEAY 

Source / Source

2005, vol. 46, n^o51 [6 page(s) (article)], [Note(s): 8819,8931-8935 [6 p.]]

Langue / Language

Anglais

Editeur / Publisher

Elsevier, Oxford, ROYAUME-UNI  (1959) (Revue)

Mots-clés d'auteur / Author Keywords

Thioethers ; Thiols ; Alkyl halides ; Cesium carbonate ; Tetrabutylammonium iodide ;

Localisation / Location

INIST-CNRS, Cote INIST : 8899 B, 35400013510806.0260